https://www.spreaker.com/podcast/the-disciplined-troublemakers--5927126enBusinessCopyright Heartcast Mediahttps://d3wo5wojvuv7l.cloudfront.net/t_rss_itunes_square_1400/images.spreaker.com/original/471908582b5e37e5186d836ec6e308cf.jpghttps://www.spreaker.com/podcast/the-disciplined-troublemakers--5927126Sun, 12 Jul 2026 21:34:01 +0000Scott ShagoryScott Shagoryfeeds@spreaker.comThe Disciplined Troublemakers Podcast is a weekly show exploring how technology CEOs and their teams are scaling, expand profitability, and exiting their companies – on their terms. Hosted by Scott Shagory, Disciplined Troublemakers is designed to...falseepisodichttps://purplefinchgroup.com/podcast/embedding-security-as-a-growth-engine-with-jon-mclachlan/What if your security program was your best sales tool?

Most B2B SaaS founders treat security as a cost center, something to minimize, budget around, and deal with only when it bites them. Jon McLachlan has spent years making the case that this framing is exactly backwards, and the founders who get that earliest tend to scale the fastest.

This episode gets into the real mechanics of scaling SaaS companies with security embedded from the start, not bolted on. For technology CEOs and operators weighing build versus buy decisions, the conversation around fractional security teams versus in-house hiring is one of the most honest you will hear on the topic of B2B software scaling.

Jon McLachlan is the CEO and co-founder of Ysecurity.io, where he helps SaaS companies build practical embedded security and compliance programs without slowing down product development. He also leads Cyberbase AI, focused on the intersection of AI and cybersecurity, and co-hosts the Security Podcast of Silicon Valley, now over 90 episodes deep. Jon started Ysecurity almost by accident, helping founder friends who needed security guidance, and grew the team to more than 45 people through referrals alone.

Key Takeaways

Bootstrapping a security firm through referrals is possible when trust is the product: every client at Ysecurity has come through word of mouth, a signal that founders are handing over the keys to people they already believe in.

The fractional security team model solves a real gap in B2B software scaling: founders can rent an entire embedded security function, from vCISO to red teaming to GRC, without the complexity of building an in-house team from zero.

Checkbox security is a floor, not a ceiling: SOC 2 Type 2 and ISO certifications matter for sales cycles, but the real return on investment comes from integrating security into marketing, sales training, and product positioning so it opens new business.

Chasing enterprise clients when your DNA is startup-focused is a costly detour: Ysecurity tried repositioning for large publicly traded organizations, landed a few deals, and found the red tape incompatible with their speed and culture, a pivot that clarified everything.

Founder mental health deserves more airtime than it gets: with depression rates among tech founders estimated around 43 percent compared to roughly 9 percent in the general population, protecting personal recovery time, whether running, cycling, or scheduling unstructured space, is an operational decision, not a luxury.

Jon McLachlan said, "Security is not just this little box on the side that we should think of as a cost center. The right way to do this stuff is really to integrate it into the entire organization. It is an investment in every sense of the word, and you should expect it to pay off."

Host Scott Shagory said, "Sell security without selling security, to overgeneralize. If you can do that, it is just such a potent message, and to be able to really enable gains that are more challenging and yet at the same time provide genuine security, it is not just a checkoff list."

Timestamps
00:00 Welcome and guest introduction
01:05 Why Jon and his co-founder Sasha started Ysecurity
02:50 ICP focus: organic growth toward B2B SaaS and AI-enabled companies
03:33 Why ideal customers sometimes still say no, build versus buy
08:47 Scaling from 2 to 45 people: culture, remote work, and staying connected
12:38 Decisions that created disproportionate leverage, and the enterprise pivot mistake
15:17 Selling security as a growth engine, not a cost center
18:19 Where the market undervalues or oversimplifies embedded security
23:43 What work founders must protect: running, biking, and personal recovery
27:22 Silicon Valley pressure, 996 culture, and how Jon navigated a difficult personal period
34:49 What the next 12 to 18 months look like for Ysecurity and Cyberbase AI
37:42 Networking effects, trust, and why referrals are the whole game
42:11 Conviction, authenticity, and what the best founder relationships actually feel like
44:25 Where to connect with Jon and closing thoughts

Connect with Jon McLachlan

LinkedIn: https://www.linkedin.com/in/jonmclachlan

Ysecurity: https://www.ysecurity.io

Cyberbase AI: https://www.cyberbase.aiS

ecurity Podcast of Silicon Valley: available on major podcast platforms
]]>https://api.spreaker.com/episode/72557389Tue, 07 Jul 2026 07:25:01 +0000Scott ShagoryWhat if your security program was your best sales tool? Most B2B SaaS founders treat security as a cost center, something to minimize, budget around, and deal with only when it bites them. Jon McLachlan has spent years making the case that this...What if your security program was your best sales tool?

Most B2B SaaS founders treat security as a cost center, something to minimize, budget around, and deal with only when it bites them. Jon McLachlan has spent years making the case that this framing is exactly backwards, and the founders who get that earliest tend to scale the fastest.

This episode gets into the real mechanics of scaling SaaS companies with security embedded from the start, not bolted on. For technology CEOs and operators weighing build versus buy decisions, the conversation around fractional security teams versus in-house hiring is one of the most honest you will hear on the topic of B2B software scaling.

Jon McLachlan is the CEO and co-founder of Ysecurity.io, where he helps SaaS companies build practical embedded security and compliance programs without slowing down product development. He also leads Cyberbase AI, focused on the intersection of AI and cybersecurity, and co-hosts the Security Podcast of Silicon Valley, now over 90 episodes deep. Jon started Ysecurity almost by accident, helping founder friends who needed security guidance, and grew the team to more than 45 people through referrals alone.

Key Takeaways

Bootstrapping a security firm through referrals is possible when trust is the product: every client at Ysecurity has come through word of mouth, a signal that founders are handing over the keys to people they already believe in.

The fractional security team model solves a real gap in B2B software scaling: founders can rent an entire embedded security function, from vCISO to red teaming to GRC, without the complexity of building an in-house team from zero.

Checkbox security is a floor, not a ceiling: SOC 2 Type 2 and ISO certifications matter for sales cycles, but the real return on investment comes from integrating security into marketing, sales training, and product positioning so it opens new business.

Chasing enterprise clients when your DNA is startup-focused is a costly detour: Ysecurity tried repositioning for large publicly traded organizations, landed a few deals, and found the red tape incompatible with their speed and culture, a pivot that clarified everything.

Founder mental health deserves more airtime than it gets: with depression rates among tech founders estimated around 43 percent compared to roughly 9 percent in the general population, protecting personal recovery time, whether running, cycling, or scheduling unstructured space, is an operational decision, not a luxury.

Jon McLachlan said, "Security is not just this little box on the side that we should think of as a cost center. The right way to do this stuff is really to integrate it into the entire organization. It is an investment in every sense of the word, and you should expect it to pay off."

Host Scott Shagory said, "Sell security without selling security, to overgeneralize. If you can do that, it is just such a potent message, and to be able to really enable gains that are more challenging and yet at the same time provide genuine security, it is not just a checkoff list."

Timestamps
00:00 Welcome and guest introduction
01:05 Why Jon and his co-founder Sasha started Ysecurity
02:50 ICP focus: organic growth toward B2B SaaS and AI-enabled companies
03:33 Why ideal customers sometimes still say no, build versus buy
08:47 Scaling from 2 to 45 people: culture, remote work, and staying connected
12:38 Decisions that created disproportionate leverage, and the enterprise pivot mistake
15:17 Selling security as a growth engine, not a cost center
18:19 Where the market undervalues or oversimplifies embedded security
23:43 What work founders must protect: running, biking, and personal recovery
27:22 Silicon Valley pressure, 996 culture, and how Jon navigated a difficult...]]>2874aicybersecurity,b2bsaassecurity,buildversusbuy,cyberbaseai,cybersecurityforfounders,embeddedsecurity,foundermentalhealth,fractionalciso,isocertification,referraldrivengrowth,saascompliance,saasscaling,securityasgrowthengine,securitysalesenablement,siliconvalleystartups,soc2type2,startupcybersecurity,trustcenterstrategy,vciso,ysecurityfalsefullhttps://purplefinchgroup.com/podcast/when-dcim-infrastructure-starts-to-think-with-jad-jebara/
Jad’s path runs through two corporate turnarounds—at Peer 1 Hosting, where disciplined execution helped drive a $650MM acquisition by Cogeco, and at IDS Software, which was acquired by PDF Solutions. He’s led finance, supply chain, and IT; run a consulting firm on ERP and process design; and built a career at the intersection of finance and technology. That background now fuels Hyperview’s product-led approach: self-serve deployment, transparent pricing, and global scale without the bloat.

In this conversation, Scott follows the thread from problem to practice: how operators move from scattered systems to a single source of truth; how data center teams balance utilization, ESG, and AI-era demand; and how a CEO’s four Rs—responsibility, realism, reflection, and resilience—shape decisions when the stakes are high.

If you work in or around critical infrastructure, this story offers a practical map: what to measure, how to act, and how to lead when growth arrives all at once. Press play.

Chapters:

00:00 - Intro
00:09 - Entrepreneurship, Scaling, and Insights
03:50 - "Reinventing DCIM for Sustainable Infrastructure"
07:41 - Data Centers and Rising Costs
10:43 - Scaling for Global Data Solutions
16:51 - "Optimizing Industry Sustainability Metrics"
20:54 - Comprehensive Infrastructure Monitoring Solution
23:33 - "Clear AI Roadmap and Vision"
25:40 - "Product-Led Growth and Strategy"
30:44 - Complexity in Tech and Strategy
34:56 - Founder Challenges and Growth Insights
37:19 - Driving Network, AI, and Growth
42:19 - AI's Impact and Leadership Evolution
45:34 - Reflection, Responsibility, Resilience
48:43 - "Empathy and a Learner Mindset"
51:15 - "Discipline Troublemakers Podcast Outro"
51:26 - Outro

Quotes:

"Make critical infrastructure think. Build the tools we needed. With vision and a learner’s mindset, curiosity becomes an impact."- Jad Jebara

"Make the complex simple so others can win. Trust, clarity, and connection matter as much as the tech."- Scott Shagory

Key Takeaways:

From Frustration to Innovation
Making Critical Infrastructure Think
Redefining Data Center Management
Scaling Globally, Collaborating Locally
Sustainability With Real Impact
Leading With Joy and Resilience
Product Led, Customer Driven

Connect with the Guest: Jad Jebara
LinkedIn: https://www.linkedin.com/in/jadjebara/
Website:https://hyperviewhq.com/

Connect with the Host: Scott Shagory
Website: http://purplefinchgroup.com
LinkedIn: http://linkedin.com/in/scottshagory
Email: scott@purplefinchgroup.com

Sponsor: Purple Flinch Group
https://www.purplefinchgroup.com/

Powered by:http://heartcastmedia.com/]]>https://api.spreaker.com/episode/68777805Tue, 06 Jan 2026 07:30:08 +0000Scott ShagoryScott Shagory opens Disciplined Troublemakers with a scene many leaders know well: complex infrastructure, rising costs, and the pressure to scale without surprises. Across the table sits Jad Jebara, the co-founder, President, and CEO of Hyperview,...
Jad’s path runs through two corporate turnarounds—at Peer 1 Hosting, where disciplined execution helped drive a $650MM acquisition by Cogeco, and at IDS Software, which was acquired by PDF Solutions. He’s led finance, supply chain, and IT; run a consulting firm on ERP and process design; and built a career at the intersection of finance and technology. That background now fuels Hyperview’s product-led approach: self-serve deployment, transparent pricing, and global scale without the bloat.

In this conversation, Scott follows the thread from problem to practice: how operators move from scattered systems to a single source of truth; how data center teams balance utilization, ESG, and AI-era demand; and how a CEO’s four Rs—responsibility, realism, reflection, and resilience—shape decisions when the stakes are high.

If you work in or around critical infrastructure, this story offers a practical map: what to measure, how to act, and how to lead when growth arrives all at once. Press play.

Chapters:

00:00 - Intro
00:09 - Entrepreneurship, Scaling, and Insights
03:50 - "Reinventing DCIM for Sustainable Infrastructure"
07:41 - Data Centers and Rising Costs
10:43 - Scaling for Global Data Solutions
16:51 - "Optimizing Industry Sustainability Metrics"
20:54 - Comprehensive Infrastructure Monitoring Solution
23:33 - "Clear AI Roadmap and Vision"
25:40 - "Product-Led Growth and Strategy"
30:44 - Complexity in Tech and Strategy
34:56 - Founder Challenges and Growth Insights
37:19 - Driving Network, AI, and Growth
42:19 - AI's Impact and Leadership Evolution
45:34 - Reflection, Responsibility, Resilience
48:43 - "Empathy and a Learner Mindset"
51:15 - "Discipline Troublemakers Podcast Outro"
51:26 - Outro

Quotes:

"Make critical infrastructure think. Build the tools we needed. With vision and a learner’s mindset, curiosity becomes an impact."- Jad Jebara

"Make the complex simple so others can win. Trust, clarity, and connection matter as much as the tech."- Scott Shagory

Key Takeaways:

From Frustration to Innovation
Making Critical Infrastructure Think
Redefining Data Center Management
Scaling Globally, Collaborating Locally
Sustainability With Real Impact
Leading With Joy and Resilience
Product Led, Customer Driven

Connect with the Guest: Jad Jebara
LinkedIn: https://www.linkedin.com/in/jadjebara/
Website:https://hyperviewhq.com/

Connect with the Host: Scott Shagory
Website: http://purplefinchgroup.com
LinkedIn: http://linkedin.com/in/scottshagory
Email: scott@purplefinchgroup.com

Sponsor: Purple Flinch Group
https://www.purplefinchgroup.com/

Powered by:http://heartcastmedia.com/]]>3128aiindatacenters,ceoleadershiplessons,cloudnativedcim,criticalinfrastructure,datacenterinfrastructuremanage,dcimmodernization,digitaltwinmonitoring,disciplinedtroublemakerspodcas,energyefficiencyandpowerutiliz,enterpriseinfrastructurescalin,entrepreneurshipandturnarounds,financemeetstechnology,fourrsofleadership,globalcolocationproviders,hyperviewplatform,industrialiotanddcim,networkandsensortelemetry,productledgrowth,saasfordatacenters,sustainabilityandesgfalsefullhttps://purplefinchgroup.com/podcast/how-badger-maps-scaled-to-8m-arr-w-o-vc-fuel/
Scott and Steve share an insightful conversation about the realities of scaling a SaaS business without the backing of venture capital. They discuss how actively listening to customer feedback helped shape Badger Maps' unique niche in the market. Steve also sheds light on the significance of memorable branding—yes, it often involves an animal!

This episode offers valuable insights on remote team dynamics, achieving product-market fit, and the merits of steady growth over the rapid pace often associated with VC-funded ventures. Founders, CEOs, and anyone interested in sustainable technology growth will find pragmatic lessons and candid reflections throughout their discussion.

Chapters:

00:00 - Introduction
00:19 - From Sales to Software Startup
06:00 - Naming Trends in Tech Branding
08:14 - Global Team Structure Insights
12:37 - Classic SaaS Success Journey
14:18 - AI Success and Scaling Challenges
19:28 - Strategic Decisions and Market Insights
23:52 - Building Differentiation Through Hard Work
25:51 - Focus Over Ego in Business
30:47 - Sales Mapping and Territory Tools
33:34 - Bootstrap Success Through Customer Focus
34:46 - Competing in Mapping Solutions
40:58 - Tech Priorities: Team, Product, Growth
44:10 - Strategic Foundations for Sustained Growth
46:59 - Early Entrepreneurship and App Building
49:35 - Bliss in Ignorance
52:54 - Incentives Shape Outcomes
56:29 - Outro

Quotes:

"Identify a niche and deliver real value. With software's extensibility, steady growth and customer focus can lead to lasting success."- Steve Benson

"Consistency in serving customers is key. Stay true to your vision, listen carefully, and you'll create something truly impactful."- Scott Shagory

Key Takeaways:

Solve Problems You Know Deeply
Creativity Isn’t Always About Reinventing the Wheel
Steady, Sustainable Growth Can Win the Race
Listen to Your Customers—And Build Moats Around Their Challenges
Know Your Strengths and Stay In Your Lane
Bootstrapping vs. VC: There’s No One-Size-Fits-All Path
You Will Grow, Even If You Don’t Expect To
Endurance Builds Brands That Matter

Connect with Steve Benson
LinkedIn: https://www.linkedin.com/in/stevenbenson/
Instagram: Steve Benson (@stevebensonsf)
Website: Badger Maps - Route Planner for Sales

Connect with the Host Scott Shagory
http://purplefinchgroup.com
http://linkedin.com/in/scottshagory
Email: scott@purplefinchgroup.com

Sponsor: Purple Flinch Group
https://www.purplefinchgroup.com/

Powered by:http://heartcastmedia.com/]]>https://api.spreaker.com/episode/68364650Tue, 02 Dec 2025 07:25:07 +0000Scott ShagoryWelcome back to Disciplined Troublemakers. In this episode, host Scott Shagory engages with Steve Benson, the CEO and founder of Badger Maps, a leading mobile mapping solution tailored for field sales professionals. Steve’s journey from tech sales to...
Scott and Steve share an insightful conversation about the realities of scaling a SaaS business without the backing of venture capital. They discuss how actively listening to customer feedback helped shape Badger Maps' unique niche in the market. Steve also sheds light on the significance of memorable branding—yes, it often involves an animal!

This episode offers valuable insights on remote team dynamics, achieving product-market fit, and the merits of steady growth over the rapid pace often associated with VC-funded ventures. Founders, CEOs, and anyone interested in sustainable technology growth will find pragmatic lessons and candid reflections throughout their discussion.

Chapters:

00:00 - Introduction
00:19 - From Sales to Software Startup
06:00 - Naming Trends in Tech Branding
08:14 - Global Team Structure Insights
12:37 - Classic SaaS Success Journey
14:18 - AI Success and Scaling Challenges
19:28 - Strategic Decisions and Market Insights
23:52 - Building Differentiation Through Hard Work
25:51 - Focus Over Ego in Business
30:47 - Sales Mapping and Territory Tools
33:34 - Bootstrap Success Through Customer Focus
34:46 - Competing in Mapping Solutions
40:58 - Tech Priorities: Team, Product, Growth
44:10 - Strategic Foundations for Sustained Growth
46:59 - Early Entrepreneurship and App Building
49:35 - Bliss in Ignorance
52:54 - Incentives Shape Outcomes
56:29 - Outro

Quotes:

"Identify a niche and deliver real value. With software's extensibility, steady growth and customer focus can lead to lasting success."- Steve Benson

"Consistency in serving customers is key. Stay true to your vision, listen carefully, and you'll create something truly impactful."- Scott Shagory

Key Takeaways:

Solve Problems You Know Deeply
Creativity Isn’t Always About Reinventing the Wheel
Steady, Sustainable Growth Can Win the Race
Listen to Your Customers—And Build Moats Around Their Challenges
Know Your Strengths and Stay In Your Lane
Bootstrapping vs. VC: There’s No One-Size-Fits-All Path
You Will Grow, Even If You Don’t Expect To
Endurance Builds Brands That Matter

Connect with Steve Benson
LinkedIn: https://www.linkedin.com/in/stevenbenson/
Instagram: Steve Benson (@stevebensonsf)
Website: Badger Maps - Route Planner for Sales

Connect with the Host Scott Shagory
http://purplefinchgroup.com
http://linkedin.com/in/scottshagory
Email: scott@purplefinchgroup.com

Sponsor: Purple Flinch Group
https://www.purplefinchgroup.com/

Powered by:http://heartcastmedia.com/]]>3439badgermaps,bootstrappedsaas,customerdrivendevelopment,disciplinedtroublemakerspodcas,fieldsalessoftware,gridsquid,namingtechcompanies,nonvcgrowth,productmarketfit,remoteglobalteams,saasfounderstories,saasleadershipinsights,salesmappingtools,scalingsoftwarecompanies,scottshagory,startupbrandingstrategy,startupfounderlessons,stevebenson,sustainablestartupgrowth,techentrepreneurshipfalsefullhttps://purplefinchgroup.com/podcast/your-financial-story-is-powerful-with-pam-prior/
Scott and Pam discuss how tech CEOs, whether bootstrapped or funded, can refine their financial storytelling and address challenges that arise from overlooked financials. Pam shares practical advice on establishing reliable bookkeeping practices, balancing growth with profitability, developing effective pricing models, and determining the right time to bring in a CFO or restructure the team.

For those experiencing uncertainty in their business finances or seeking to implement processes that support sustainable growth, this conversation offers valuable insights and actionable strategies. Learn how to achieve financial clarity and make informed decisions that drive your business forward.

Pam Prior is the owner of a bookkeeping and fractional CFO company, a two-time bestselling author, and the host of the Cash Flow and She Said, She Said podcasts. Known as the "Finance Friend in a Foxhole," she is dedicated to supporting 21st-century entrepreneurs.

Chapters:

00:00 – Introduction
01:03 – "Numbers Reveal Business Story"
05:26 – Financial Literacy: Key to Business Success
09:15 – Early Stage Business Strategy
10:55 – Diversify Investments, Understand Cash Flow
16:11 – Pricing Strategy for Niche Coaching
18:58 – Value over Price
20:02 – "Charging Difficult Clients More"
26:23 – Scaling Beyond Founder Limits
28:29 – Scaling Challenges and Leadership Transition
33:15 – "Importance of Client Contracts"
34:12 – Founder to CEO: Prioritize Roles
38:27 – Family Dynamics in Business Hierarchies
43:04 – Evolving Documentation Practices
45:35 – "When to Hire a CFO"
49:04 – CFO Role in Business Strategy
51:01 – Embracing Entrepreneurial Agility
54:34 – Interview with Pam on YouTube
54:55 – Outro

Quotes:

"Seeing your numbers as your business story clears the fog of uncertainty. That clarity brings true freedom."- Pam Prior

"When uncertainty lifts, clarity and perspective bring confidence and limitless growth."- Scott Shagory

Key Takeaways:

Financials Are Your Business Story, Not Just Numbers
Clean Books Are Cheaper (and Less Stressful) than Cleanups
Lift the Fog: Clarity Equals Confidence
For Bootstrappers: Profit, Scale, and Personal Goals Must Be Balanced
Scaling from $1M to $5M Means Reinventing Processes—and Yourself
Process = Freedom, Not Handcuffs
A CFO Is Your Foxhole Ally, Not Just a Number Cruncher

Connect with Pam Prior

LinkedIn: https://www.linkedin.com/in/pamsprior
Website: https://pamprior.com/

Connect with the Host Scott Shagory:

http://purplefinchgroup.com
http://linkedin.com/in/scottshagory
Email: scott@purplefinchgroup.com

Sponsor: Purple Flinch Group
https://www.purplefinchgroup.com/

Powered by: http://heartcastmedia.com/]]>https://api.spreaker.com/episode/66886339Tue, 22 Jul 2025 07:05:07 +0000Scott ShagoryIn this episode of Disciplined Troublemakers, host Scott Shagory sits down with Pam Prior, a CFO and financial coach with over 30 years of experience. Pam has guided a diverse range of clients, including bootstrapped entrepreneurs, private equity...
Scott and Pam discuss how tech CEOs, whether bootstrapped or funded, can refine their financial storytelling and address challenges that arise from overlooked financials. Pam shares practical advice on establishing reliable bookkeeping practices, balancing growth with profitability, developing effective pricing models, and determining the right time to bring in a CFO or restructure the team.

For those experiencing uncertainty in their business finances or seeking to implement processes that support sustainable growth, this conversation offers valuable insights and actionable strategies. Learn how to achieve financial clarity and make informed decisions that drive your business forward.

Pam Prior is the owner of a bookkeeping and fractional CFO company, a two-time bestselling author, and the host of the Cash Flow and She Said, She Said podcasts. Known as the "Finance Friend in a Foxhole," she is dedicated to supporting 21st-century entrepreneurs.

Chapters:

00:00 – Introduction
01:03 – "Numbers Reveal Business Story"
05:26 – Financial Literacy: Key to Business Success
09:15 – Early Stage Business Strategy
10:55 – Diversify Investments, Understand Cash Flow
16:11 – Pricing Strategy for Niche Coaching
18:58 – Value over Price
20:02 – "Charging Difficult Clients More"
26:23 – Scaling Beyond Founder Limits
28:29 – Scaling Challenges and Leadership Transition
33:15 – "Importance of Client Contracts"
34:12 – Founder to CEO: Prioritize Roles
38:27 – Family Dynamics in Business Hierarchies
43:04 – Evolving Documentation Practices
45:35 – "When to Hire a CFO"
49:04 – CFO Role in Business Strategy
51:01 – Embracing Entrepreneurial Agility
54:34 – Interview with Pam on YouTube
54:55 – Outro

Quotes:

"Seeing your numbers as your business story clears the fog of uncertainty. That clarity brings true freedom."- Pam Prior

"When uncertainty lifts, clarity and perspective bring confidence and limitless growth."- Scott Shagory

Key Takeaways:

Financials Are Your Business Story, Not Just Numbers
Clean Books Are Cheaper (and Less Stressful) than Cleanups
Lift the Fog: Clarity Equals Confidence
For Bootstrappers: Profit, Scale, and Personal Goals Must Be Balanced
Scaling from $1M to $5M Means Reinventing Processes—and Yourself
Process = Freedom, Not Handcuffs
A CFO Is Your Foxhole Ally, Not Just a Number Cruncher

Connect with Pam Prior

LinkedIn: https://www.linkedin.com/in/pamsprior
Website: https://pamprior.com/

Connect with the Host Scott Shagory:

http://purplefinchgroup.com
http://linkedin.com/in/scottshagory
Email: scott@purplefinchgroup.com

Sponsor: Purple Flinch Group
https://www.purplefinchgroup.com/

Powered by: http://heartcastmedia.com/]]>3338bookkeepingbestpractices,bootstrappedfounders,businessstorytelling,cashflowmanagement,cfoinsights,earlystagestartups,entrepreneurialfinance,financialclarity,financialstrategy,foundertoceo,fractionalcfo,growthvs.profitability,hiringacfo,leadershiptransition,nichecoaching,pamprior,pricingstrategy,scalingbusiness,scottshagory,techceosfalsefullhttps://purplefinchgroup.com/podcast/scaling-without-breaking-what-makes-you-great-with-desh-urs/
The conversation explores the pressing challenges tech companies face in a swiftly evolving environment, focusing on effective data management, the accelerating advancements in AI, and maintaining security in critical industries. Desh discusses strategies for navigating uncertainty, the importance of enduring customer relationships, and the significance of adhering to core company values amidst growth.

Listeners will hear detailed accounts of iBridge 's expansion into international markets like Saudi Arabia, the transition from service-oriented to product-driven models, and how prioritizing both employees and clients has been pivotal to the company's sustained success. This episode provides actionable insights and practical wisdom for CEOs, entrepreneurs, and anyone interested in the transformative role of technology in various industries.

Desh Urs brings a wealth of experience from leading roles at TransUnion, Silicon Graphics, and Acxiom Corp., positioning him as a knowledgeable voice in digital transformation and business scaling.

Chapters:

00:00 - Introduction
01:06 - Understanding and Organizing Data Value
03:22 - Prioritizing Foundational Questions in AI
06:58 - Data Expertise and Security Challenges
12:53 - Saudi Arabia's Social Transformation
14:32 - Rapid Economic Transformation Ahead
17:23 - Customer-Centric Partnership Success Model
22:10 - Customer Trust Ensures Mutual Success
24:21 - Terminating Contract with CEO
28:44 - Conversation Encouragement for Team Awareness
31:04 - Navigating Information Overload Challenges
36:11 - Transitioning from Services to Product
38:13 - Leadership and Transition in Challenges
43:03 - Decision-Making in a Flat Organization
45:08 - Transformative Social Impact of Connectivity
48:12 - Recruitment and Communication Strategy
50:11 - Outro

Quotes:

"Prioritize your customers, understand your true purpose, and embrace vulnerability. That's how we grow together."- Desh Urs

"Ask who you are and who you serve. In a fast-paced world, wisdom comes from reflection and staying true to your mission."- Scott Shagory

Key Takeaways:

Transformation Starts with Understanding Your Data
Adaptability is Essential in an Era of Rapid Change
Security & Trust are Non-Negotiable
Scaling Means Embracing Uncertainty—But Moving Forward Anyway
Partnerships Over Transactions
True Value Lies in Relationships and Integrity
Evolving from Services to Products
Purpose Beyond Profit
Leadership is About Vulnerability and Openness

Connect with Desh Urs:

LinkedIn: https://www.linkedin.com/in/deshurs/
Website:Home - iBridge LLC

Connect with the Host Scott Shagory:

http://purplefinchgroup.com
http://linkedin.com/in/scottshagory
Email: mailto:scott@purplefinchgroup.com

Sponsor: Purple Flinch Group
https://www.purplefinchgroup.com/

Powered by:http://heartcastmedia.com/]]>https://api.spreaker.com/episode/66581949Tue, 08 Jul 2025 07:25:07 +0000Scott ShagoryWelcome back to the Disciplined Troublemakers podcast. In today’s episode, host Scott Shagory engages with Desh Urs, founder and CEO of iBridge —a global leader in digital transformation within healthcare, legal services, utilities, and defense...
The conversation explores the pressing challenges tech companies face in a swiftly evolving environment, focusing on effective data management, the accelerating advancements in AI, and maintaining security in critical industries. Desh discusses strategies for navigating uncertainty, the importance of enduring customer relationships, and the significance of adhering to core company values amidst growth.

Listeners will hear detailed accounts of iBridge 's expansion into international markets like Saudi Arabia, the transition from service-oriented to product-driven models, and how prioritizing both employees and clients has been pivotal to the company's sustained success. This episode provides actionable insights and practical wisdom for CEOs, entrepreneurs, and anyone interested in the transformative role of technology in various industries.

Desh Urs brings a wealth of experience from leading roles at TransUnion, Silicon Graphics, and Acxiom Corp., positioning him as a knowledgeable voice in digital transformation and business scaling.

Chapters:

00:00 - Introduction
01:06 - Understanding and Organizing Data Value
03:22 - Prioritizing Foundational Questions in AI
06:58 - Data Expertise and Security Challenges
12:53 - Saudi Arabia's Social Transformation
14:32 - Rapid Economic Transformation Ahead
17:23 - Customer-Centric Partnership Success Model
22:10 - Customer Trust Ensures Mutual Success
24:21 - Terminating Contract with CEO
28:44 - Conversation Encouragement for Team Awareness
31:04 - Navigating Information Overload Challenges
36:11 - Transitioning from Services to Product
38:13 - Leadership and Transition in Challenges
43:03 - Decision-Making in a Flat Organization
45:08 - Transformative Social Impact of Connectivity
48:12 - Recruitment and Communication Strategy
50:11 - Outro

Quotes:

"Prioritize your customers, understand your true purpose, and embrace vulnerability. That's how we grow together."- Desh Urs

"Ask who you are and who you serve. In a fast-paced world, wisdom comes from reflection and staying true to your mission."- Scott Shagory

Key Takeaways:

Transformation Starts with Understanding Your Data
Adaptability is Essential in an Era of Rapid Change
Security & Trust are Non-Negotiable
Scaling Means Embracing Uncertainty—But Moving Forward Anyway
Partnerships Over Transactions
True Value Lies in Relationships and Integrity
Evolving from Services to Products
Purpose Beyond Profit
Leadership is About Vulnerability and Openness

Connect with Desh Urs:

LinkedIn: https://www.linkedin.com/in/deshurs/
Website:Home - iBridge LLC

Connect with the Host Scott Shagory:

http://purplefinchgroup.com
http://linkedin.com/in/scottshagory
Email: mailto:scott@purplefinchgroup.com

Sponsor: Purple Flinch Group
fullhttps://purplefinchgroup.com/podcast/traceable-role-aware-ai-transforming-financial-operations-with-tom-blair/http://iCLERK.AI . Tom brings decades of expertise in AI, data, and enterprise technology, highlighted by successful ventures with Performance Livestock Analytics and ClearAg.

Scott and Tom examine the impact of applied AI on enterprise operations, focusing on how iCLERK optimizes intricate, repetitive workflows in the financial sector through role-aware autonomous agents. Drawing from his extensive experience, Tom discusses the convergence of AI with long-held ideas and how the swift advancements in technology are opening doors for businesses willing to adapt.

Join the conversation as they address the practical challenges and milestones of AI integration, the significance of operational collaborations, and the implications of AI's rapid growth on organizational efficiency, workforce structure, and leadership strategies. For an insightful look into the progression of AI-driven business solutions, this episode provides valuable perspectives.

Chapters:

00:00 - Introduction
00:09 - Automating Financial Reporting with AI
06:04 - Streamlining Workflows in IT Industry
08:17 - "Traceable AI for Reliable Reporting"
10:13 - Career Highlights in AI and Analytics
15:00 - "Tech's Emotional Relief Paradox"
18:48 - Deep Institutional Knowledge in Finance
20:13 - Misconceptions in AI Implementation
24:37 - Leveraging AI for Efficient Learning
27:14 - Joyful Life and Intellectual Fulfillment
32:31 - Early Vision: Semantic Image Recognition
33:43 - Bridging Tech Evolution & Human Static
37:58 - "Startups, Technology, and Happiness Curve"
40:06 - "Quick Results Through Clear Purpose"
42:36 - Outro

Quotes:

"Curiosity drives innovation. Solving real problems brings value and joy."- Tom Blair

"Enhancing a single workflow transforms everything. Technology is about progress and simplicity."- Scott Shagory

Key Takeaways:

Reinventing Professional Workflows, One Agent at a Time
From Fear to Opportunity: AI Adoption Is Accelerating
Scaling Smarter, Not Harder
Depth Matters: Institutional Knowledge as Secret Sauce
AI Implementation Without Disruption
The Joy of Building—and Continuous Learning
The Exponential Future Is Now
Start With Small Steps—And Unlock Big Change

Connect with Tom Blair

LinkedIn: linkedin.com/in/tom-blair
Website: http://www.iclerk.ai

Connect with the Host Scott Shagory:

http://purplefinchgroup.com
http://linkedin.com/in/scottshagory
Email: scott@purplefinchgroup.com

Sponsor: Purple Flinch Group
https://www.purplefinchgroup.com/

Powered by: http://heartcastmedia.com/]]>https://api.spreaker.com/episode/66018304Tue, 03 Jun 2025 07:30:10 +0000Scott ShagoryWelcome back to the Disciplined Troublemakers podcast, a space dedicated to navigating the complexities of scaling technology companies with increased efficiency and reduced strain. In this episode, host Scott Shagory engages with Tom Blair, cofounder...http://iCLERK.AI . Tom brings decades of expertise in AI, data, and enterprise technology, highlighted by successful ventures with Performance Livestock Analytics and ClearAg.

Scott and Tom examine the impact of applied AI on enterprise operations, focusing on how iCLERK optimizes intricate, repetitive workflows in the financial sector through role-aware autonomous agents. Drawing from his extensive experience, Tom discusses the convergence of AI with long-held ideas and how the swift advancements in technology are opening doors for businesses willing to adapt.

Join the conversation as they address the practical challenges and milestones of AI integration, the significance of operational collaborations, and the implications of AI's rapid growth on organizational efficiency, workforce structure, and leadership strategies. For an insightful look into the progression of AI-driven business solutions, this episode provides valuable perspectives.

Chapters:

00:00 - Introduction
00:09 - Automating Financial Reporting with AI
06:04 - Streamlining Workflows in IT Industry
08:17 - "Traceable AI for Reliable Reporting"
10:13 - Career Highlights in AI and Analytics
15:00 - "Tech's Emotional Relief Paradox"
18:48 - Deep Institutional Knowledge in Finance
20:13 - Misconceptions in AI Implementation
24:37 - Leveraging AI for Efficient Learning
27:14 - Joyful Life and Intellectual Fulfillment
32:31 - Early Vision: Semantic Image Recognition
33:43 - Bridging Tech Evolution & Human Static
37:58 - "Startups, Technology, and Happiness Curve"
40:06 - "Quick Results Through Clear Purpose"
42:36 - Outro

Quotes:

"Curiosity drives innovation. Solving real problems brings value and joy."- Tom Blair

"Enhancing a single workflow transforms everything. Technology is about progress and simplicity."- Scott Shagory

Key Takeaways:

Reinventing Professional Workflows, One Agent at a Time
From Fear to Opportunity: AI Adoption Is Accelerating
Scaling Smarter, Not Harder
Depth Matters: Institutional Knowledge as Secret Sauce
AI Implementation Without Disruption
The Joy of Building—and Continuous Learning
The Exponential Future Is Now
Start With Small Steps—And Unlock Big Change

Connect with Tom Blair

LinkedIn: linkedin.com/in/tom-blair
Website: http://www.iclerk.ai

Connect with the Host Scott Shagory:

http://purplefinchgroup.com
http://linkedin.com/in/scottshagory
Email: scott@purplefinchgroup.com

Sponsor: Purple Flinch Group
https://www.purplefinchgroup.com/

Powered by: http://heartcastmedia.com/]]>2560aidriveroperations,aiintegration,appliedai,businesseffiency,enterpriseautomation,financialtech,roleawareagents,workflowoptimizationfalsefullhttps://purplefinchgroup.com/podcast/scaling-uploadcare-and-navigating-a-successful-exit-without-regrets-with-igor-debatur/
The company was acquired by Tiugo Technologies in 2024. Tiugo is a development platform focused on PLG as a GTM and is an affiliate of PSG Equity, a PE buyout firm specializing in mid-market SW companies.

Earlier in his career, Igor founded Riders - an app that helped a million users improve 15 action sports disciplines – such as skateboarding and skiing.

In this episode of The Disciplined Troublemakers podcast, host Scott Shagory engages with Igor to explore the journey of building Uploadcare. They discuss the challenges of the “build vs. buy” decision that CTOs often face, the complexities of managing large-scale file operations for diverse clients, and the strategies for handling unexpected data surges and expanding into international markets. Igor also shares his experience of selling Uploadcare to a private equity firm while preserving the company's mission and maintaining his role as CEO.

This conversation offers valuable insights for founders, technical leaders, and anyone interested in the inner workings of successful SaaS businesses. Discover practical lessons on scaling, leadership, and navigating the evolving tech landscape on The Disciplined Troublemakers.

Chapters:

00:00 - Introduction
01:23 - Tech Scaling Insights with Igor Debatore
05:28 - "Scaling Data Movement Challenges"
08:12 - Forecasting Growth Amid Uncertainty
10:46 - Cloud Platforms' Global Multi-Tenancy Operations
15:41 - Challenges Selling Solutions to Engineers
17:53 - Scaling Challenges in Networking
22:21 - "Founder Experience: Selling a Startup"
26:51 - Finding the Right Financial Partner
27:50 - Positive Experience & Learning Opportunity
31:50 - Reflecting on CEO Journey Transformation
34:24 - Human Connection: A Powerful Catalyst
37:39 - Outro

Quotes:

"I thrive on creating for people and witnessing the joy it brings our team and users. This passion fuels me every day."- Igor Debatur

"Passion projects, where you dive in and take initiative, often spark the greatest impact and fulfillment."- Scott Shagory

Key Takeaways:

Solving Unseen Problems at Scale
From Engineer to Global CEO
Build vs. Buy—Lessons Learned the Hard Way
Automatic Scaling, Real-World Resilience
Acquisition as a Strategic Step, not an End
Staying True to the Core Motivation
The Power of Community and Learning
Advice for Founders and CEOs

Connect with Igor Debatur

LinkedIn: https://linkedin.com/in/debatur
Website: https://uploadcare.com

Connect with the Host Scott Shagory:

http://purplefinchgroup.com
http://linkedin.com/in/scottshagory
Email: mailto:scott@purplefinchgroup.com

Sponsor: Purple Flinch Group
https://www.purplefinchgroup.com/

Powered by: http://heartcastmedia.com/]]>https://api.spreaker.com/episode/65703118Tue, 27 May 2025 08:00:07 +0000Scott ShagoryIgor is the co-founder and CEO of Uploadcare. Founded in 2012, Uploadcare is a file loader, data handler, and Content Delivery Network (CDN) – which ensures data is uploaded w/security, compliance, reliable storage, and a friendly UI. The company’s...
The company was acquired by Tiugo Technologies in 2024. Tiugo is a development platform focused on PLG as a GTM and is an affiliate of PSG Equity, a PE buyout firm specializing in mid-market SW companies.

Earlier in his career, Igor founded Riders - an app that helped a million users improve 15 action sports disciplines – such as skateboarding and skiing.

In this episode of The Disciplined Troublemakers podcast, host Scott Shagory engages with Igor to explore the journey of building Uploadcare. They discuss the challenges of the “build vs. buy” decision that CTOs often face, the complexities of managing large-scale file operations for diverse clients, and the strategies for handling unexpected data surges and expanding into international markets. Igor also shares his experience of selling Uploadcare to a private equity firm while preserving the company's mission and maintaining his role as CEO.

This conversation offers valuable insights for founders, technical leaders, and anyone interested in the inner workings of successful SaaS businesses. Discover practical lessons on scaling, leadership, and navigating the evolving tech landscape on The Disciplined Troublemakers.

Chapters:

00:00 - Introduction
01:23 - Tech Scaling Insights with Igor Debatore
05:28 - "Scaling Data Movement Challenges"
08:12 - Forecasting Growth Amid Uncertainty
10:46 - Cloud Platforms' Global Multi-Tenancy Operations
15:41 - Challenges Selling Solutions to Engineers
17:53 - Scaling Challenges in Networking
22:21 - "Founder Experience: Selling a Startup"
26:51 - Finding the Right Financial Partner
27:50 - Positive Experience & Learning Opportunity
31:50 - Reflecting on CEO Journey Transformation
34:24 - Human Connection: A Powerful Catalyst
37:39 - Outro

Quotes:

"I thrive on creating for people and witnessing the joy it brings our team and users. This passion fuels me every day."- Igor Debatur

"Passion projects, where you dive in and take initiative, often spark the greatest impact and fulfillment."- Scott Shagory

Key Takeaways:

Solving Unseen Problems at Scale
From Engineer to Global CEO
Build vs. Buy—Lessons Learned the Hard Way
Automatic Scaling, Real-World Resilience
Acquisition as a Strategic Step, not an End
Staying True to the Core Motivation
The Power of Community and Learning
Advice for Founders and CEOs

Connect with Igor Debatur

LinkedIn: https://linkedin.com/in/debatur
Website: https://uploadcare.com

Connect with the Host Scott Shagory:

http://purplefinchgroup.com
http://linkedin.com/in/scottshagory
Email: mailto:scott@purplefinchgroup.com

Sponsor: Purple Flinch Group
https://www.purplefinchgroup.com/

Powered by: http://heartcastmedia.com/]]>2264buildvsbuy,compliance,contentdeliverynetwork,contentmoderation,datahandling,datasecurity,developmentteams,devops,ecommerce,fileuploads,malwaredetection,saasscalingfalsefullhttps://purplefinchgroup.com/podcast/digitizing-the-convenience-stores-tech-left-behind-with-jason-vego/
Prior to Bevz, Jason founded a dog grooming SW platform, which failed, and earlier in his career he worked at Citrix as Head of Global Employee Communications and Engagemen

The conversation highlights Bevz's evolution into a comprehensive inventory management system, enabling stores to efficiently track and sell products both in-store and online. Jason discusses the unique challenges of catering to independently operated stores and outlines the company's ambitious growth plans to expand across thousands of U.S. locations. This episode provides actionable insights for technology leaders and retail enthusiasts aiming to scale their businesses and navigate the complexities of the modern marketplace.

Chapters:

00:00 - Introduction
00:09 - Convenience Store Digital Transformation Platform
03:22 - Independent Rural Store Challenges
08:45 - Protein Bar Market Challenges
11:39 - Holistic Approach to Business Growth
15:54 - Snack Food Trends and Market Insights
19:32 - "Building Trust Through Data Insights"
22:54 - "Emphasizing the Human Element in AI"
27:01 - Convenience Retail's E-Commerce Potential
28:14 - Mobile Device Impact on Ordering
32:12 - Scaling Solutions for Tech CEOs
34:09 - Balancing Excel and People Dynamics
40:10 - Leadership Growth and Challenges
41:54 - Value of Fundraising Experience
45:27 - Managing Trade-offs in Business Growth
47:45 - Outro

Quotes:

"Scaling means building trust and empowering overlooked sectors to thrive."- Scott Shagory

"We're transforming independent stores into digital powerhouses, revolutionizing convenience retail."- Jason Vego

Key Takeaways:

Unlocking Potential in the Overlooked
Building Trust and Empowering Growth
Navigating Complexity with Simplicity
Scaling with Product and People in Mind
The Human Touch in a Digital World
Visionary Yet Pragmatic

Connect with Jason Vego:
LinkedIn: https://www.linkedin.com/in/jvego/
Website: https://www.bevz.com/

Connect with the Host Scott Shagory:

http://purplefinchgroup.com
http://linkedin.com/in/scottshagory
Email: mailto:scott@purplefinchgroup.com

Sponsor: Purple Flinch Group
https://www.purplefinchgroup.com/

Powered by: http://heartcastmedia.com/]]>https://api.spreaker.com/episode/65669501Tue, 13 May 2025 08:50:07 +0000Scott ShagoryIn this episode of The Disciplined Troublemakers, host Scott Shagory welcomes Jason Vego, who is the co-founder and CEO of Bevz. Founded in 2020, Bevz is a SaaS platform for independent liquor and convenience stores, helping them centralize and...
Prior to Bevz, Jason founded a dog grooming SW platform, which failed, and earlier in his career he worked at Citrix as Head of Global Employee Communications and Engagemen

The conversation highlights Bevz's evolution into a comprehensive inventory management system, enabling stores to efficiently track and sell products both in-store and online. Jason discusses the unique challenges of catering to independently operated stores and outlines the company's ambitious growth plans to expand across thousands of U.S. locations. This episode provides actionable insights for technology leaders and retail enthusiasts aiming to scale their businesses and navigate the complexities of the modern marketplace.

Chapters:

00:00 - Introduction
00:09 - Convenience Store Digital Transformation Platform
03:22 - Independent Rural Store Challenges
08:45 - Protein Bar Market Challenges
11:39 - Holistic Approach to Business Growth
15:54 - Snack Food Trends and Market Insights
19:32 - "Building Trust Through Data Insights"
22:54 - "Emphasizing the Human Element in AI"
27:01 - Convenience Retail's E-Commerce Potential
28:14 - Mobile Device Impact on Ordering
32:12 - Scaling Solutions for Tech CEOs
34:09 - Balancing Excel and People Dynamics
40:10 - Leadership Growth and Challenges
41:54 - Value of Fundraising Experience
45:27 - Managing Trade-offs in Business Growth
47:45 - Outro

Quotes:

"Scaling means building trust and empowering overlooked sectors to thrive."- Scott Shagory

"We're transforming independent stores into digital powerhouses, revolutionizing convenience retail."- Jason Vego

Key Takeaways:

Unlocking Potential in the Overlooked
Building Trust and Empowering Growth
Navigating Complexity with Simplicity
Scaling with Product and People in Mind
The Human Touch in a Digital World
Visionary Yet Pragmatic

Connect with Jason Vego:
LinkedIn: https://www.linkedin.com/in/jvego/
Website: https://www.bevz.com/

Connect with the Host Scott Shagory:

http://purplefinchgroup.com
http://linkedin.com/in/scottshagory
Email: mailto:scott@purplefinchgroup.com

Sponsor: Purple Flinch Group
https://www.purplefinchgroup.com/

Powered by: http://heartcastmedia.com/]]>2906bevz,ceo,citrix,deliveryservice,doordash,ecommerce,inventorymanagement,saasplatform,scalingtechcompanies,ubereatsfalsefullhttps://purplefinchgroup.com/podcast/turning-cybersecurity-compliance-into-a-catalyst-with-jason-young/
In 2024 Jason and the team saved the Defense Health Agency, a Combat Support Agency w/in the U.S. DoD that supports medical services readiness for the Army, Navy, and Air Force, $25 million dollars by optimizing their cyber compliance workflows.

Chapters:
00:00 - Introduction
00:09 - Scaling Cybersecurity with Jason Young
03:48 - "From Systems Admin to Auditor"
08:01 - Cybersecurity: Cost Center or Strategic Asset?
12:35 - Transforming Conversations for Meaningful Outcomes
15:48 - Understanding Team-Specific Problems
19:37 - User-Centric Strategy for Agility
20:45 - Listening to Junior Insights
26:42 - Exploring Orchestration Layers in DOD
29:50 - Accidental CEO Journey
31:25 - Effective Leadership and Team Retention
34:16 - Rigid Systems vs. Creative Context
38:11 - Breaking Creative Blocks
43:45 - "Evolving Perceptions and Reality"
45:25 - "Meeting People Where They Are"
47:26 - Outro

Key Takeaways:
Championing Cybersecurity Compliance
Empowering IT Operations
Creating Value with Technology
Culture and Innovation Go Hand in Hand
The Power of Listening

Quotes:
"Turning compliance into a value driver can revolutionize organizations and the entire industry."- Scott Shagory

"Solving the real problem unlocks true innovation and value."- Jason Young

Connect with Jason Young:
LinkedIn: https://www.linkedin.com/in/jason-paul-young/
Website: https://pylonsecure.com

Connect with the Host Scott Shagory:
http://purplefinchgroup.com
http://linkedin.com/in/scottshagory
Email: mailto:scott@purplefinchgroup.com

Sponsor: Purple Flinch Group
https://www.purplefinchgroup.com/

Powered by: http://heartcastmedia.com/]]>https://api.spreaker.com/episode/65530078Tue, 06 May 2025 08:00:08 +0000Scott ShagoryWelcome to the Disciplined Troublemakers podcast. In today’s episode, we speak with Jason Young, founder and CEO of Pylon Cybersecurity. Jason Young is the founder and CEO of Pylon Cybersecurity, a firm he started in 2011. Pylon helps security...
In 2024 Jason and the team saved the Defense Health Agency, a Combat Support Agency w/in the U.S. DoD that supports medical services readiness for the Army, Navy, and Air Force, $25 million dollars by optimizing their cyber compliance workflows.

Chapters:
00:00 - Introduction
00:09 - Scaling Cybersecurity with Jason Young
03:48 - "From Systems Admin to Auditor"
08:01 - Cybersecurity: Cost Center or Strategic Asset?
12:35 - Transforming Conversations for Meaningful Outcomes
15:48 - Understanding Team-Specific Problems
19:37 - User-Centric Strategy for Agility
20:45 - Listening to Junior Insights
26:42 - Exploring Orchestration Layers in DOD
29:50 - Accidental CEO Journey
31:25 - Effective Leadership and Team Retention
34:16 - Rigid Systems vs. Creative Context
38:11 - Breaking Creative Blocks
43:45 - "Evolving Perceptions and Reality"
45:25 - "Meeting People Where They Are"
47:26 - Outro

Key Takeaways:
Championing Cybersecurity Compliance
Empowering IT Operations
Creating Value with Technology
Culture and Innovation Go Hand in Hand
The Power of Listening

Quotes:
"Turning compliance into a value driver can revolutionize organizations and the entire industry."- Scott Shagory

"Solving the real problem unlocks true innovation and value."- Jason Young

Connect with Jason Young:
LinkedIn: https://www.linkedin.com/in/jason-paul-young/
Website: https://pylonsecure.com

Connect with the Host Scott Shagory:
http://purplefinchgroup.com
http://linkedin.com/in/scottshagory
Email: mailto:scott@purplefinchgroup.com

Sponsor: Purple Flinch Group
https://www.purplefinchgroup.com/

Powered by: http://heartcastmedia.com/]]>2887ceo,cybercompliance,cybersecurity,dataaccuracy,defensehealthagency,federalgovernment,it,nationalsecurity,networkcompliance,techcompanies,techinnovationfalsefullhttps://purplefinchgroup.com/podcast/the-scaling-power-of-communication-at-signpost-with-lucas-wilson/
Signpost supports small and medium-sized businesses in the home service industry by streamlining day-to-day communications with prospects and customers through a unified platform. Lucas offers his perspective on the challenges and opportunities inherent in scaling a SaaS company within the home services sector, as well as the vital role of online reputation management.

Our discussion highlights the importance of quality service as a distinguishing factor and traces Signpost's path toward mastering customer communication. Lucas shares his experiences as a turnaround specialist, emphasizing the need to define a company's core identity and the impact of actively listening to customers.

Join us as we uncover the strategies and insights Lucas contributes, demonstrating why maintaining focus is crucial for growth in today’s rapidly evolving tech landscape. Whether you're a CEO, an entrepreneur, or interested in the mechanics of scaling tech companies, this episode offers valuable takeaways on pursuing progress and excellence.

Chapters:
00:00 - Introduction
01:09 - "Ensuring Quality Customer Communication"
05:53 - "AI and Live Receptionist Integration"
08:05 - Exploring AI Communication Platforms
12:18 - "Uncovering Decision-Making Insights"
15:24 - Improving Customer Service Efficiency
19:16 - Urgent Tornado Warning Tech Support
20:40 - Storytelling and Misunderstandings in Communication
26:07 - Core Values Drive Market Strategy
27:08 - Internal Reflection Drives CEO Success
31:38 - "Empowered Workforce, Secure Future"
35:34 - Enhancing Service Through Technology
36:57 - Franchise Tech Integration Challenges
40:21 - Leadership Roles: Different Mindsets
43:03 - Outro

Quotes:
"Staying focused, listening to our customers, and delivering quality service is what sets us apart."- Lucas Wilson

"Begin with the end in mind, eliminate obstacles, and build trust through seamless communication."- Scott Shagory

Key Takeaways:
Staying True to Core Values
Learning from Experience
Team Empowerment
The Journey of Transformation
Balancing AI and Human Touch
Embracing Challenges as Opportunities

Connect with Lucas Wilson:
LinkedIn: https://www.linkedin.com/in/lukewilsonsignpostceo/
Website: https://bias2action.co/

Connect with the Host Scott Shagory:
http://purplefinchgroup.com
http://linkedin.com/in/scottshagory
Email: mailto:scott@purplefinchgroup.com

Sponsor: Purple Flinch Group
https://www.purplefinchgroup.com/

Powered by: http://heartcastmedia.com/]]>https://api.spreaker.com/episode/65410290Tue, 22 Apr 2025 08:45:07 +0000Scott ShagoryWelcome to another episode of Disciplined Troublemakers, where we explore the landscape of tech companies and the art of scaling businesses effectively. Today, we are joined by Lucas Wilson, CEO of Signpost, who has been steering the company since...
Signpost supports small and medium-sized businesses in the home service industry by streamlining day-to-day communications with prospects and customers through a unified platform. Lucas offers his perspective on the challenges and opportunities inherent in scaling a SaaS company within the home services sector, as well as the vital role of online reputation management.

Our discussion highlights the importance of quality service as a distinguishing factor and traces Signpost's path toward mastering customer communication. Lucas shares his experiences as a turnaround specialist, emphasizing the need to define a company's core identity and the impact of actively listening to customers.

Join us as we uncover the strategies and insights Lucas contributes, demonstrating why maintaining focus is crucial for growth in today’s rapidly evolving tech landscape. Whether you're a CEO, an entrepreneur, or interested in the mechanics of scaling tech companies, this episode offers valuable takeaways on pursuing progress and excellence.

Chapters:
00:00 - Introduction
01:09 - "Ensuring Quality Customer Communication"
05:53 - "AI and Live Receptionist Integration"
08:05 - Exploring AI Communication Platforms
12:18 - "Uncovering Decision-Making Insights"
15:24 - Improving Customer Service Efficiency
19:16 - Urgent Tornado Warning Tech Support
20:40 - Storytelling and Misunderstandings in Communication
26:07 - Core Values Drive Market Strategy
27:08 - Internal Reflection Drives CEO Success
31:38 - "Empowered Workforce, Secure Future"
35:34 - Enhancing Service Through Technology
36:57 - Franchise Tech Integration Challenges
40:21 - Leadership Roles: Different Mindsets
43:03 - Outro

Quotes:
"Staying focused, listening to our customers, and delivering quality service is what sets us apart."- Lucas Wilson

"Begin with the end in mind, eliminate obstacles, and build trust through seamless communication."- Scott Shagory

Key Takeaways:
Staying True to Core Values
Learning from Experience
Team Empowerment
The Journey of Transformation
Balancing AI and Human Touch
Embracing Challenges as Opportunities

Connect with Lucas Wilson:
LinkedIn: https://www.linkedin.com/in/lukewilsonsignpostceo/
Website: https://bias2action.co/

Connect with the Host Scott Shagory:
http://purplefinchgroup.com
http://linkedin.com/in/scottshagory
Email: mailto:scott@purplefinchgroup.com

Sponsor: Purple Flinch Group
https://www.purplefinchgroup.com/

Powered by: http://heartcastmedia.com/]]>2588ai-driventechnology,aireceptionist,customercommunication,homeservices,innovation,omnichannel,saas,signpost,smbs,technologydevelopmentfalsefullhttps://purplefinchgroup.com/podcast/bootstrapping-plg-and-the-future-of-webinars-with-melissa-kwan/eWebinar , is transforming webinar automation by eliminating the repetitive strain of live sessions she describes as "soul crushing." In this episode of the Disciplined Troublemakers podcast, Scott Shagory explores how Melissa's innovative solutions enable technology leaders to scale their companies and boost profitability. Beyond eWebinar, Melissa cohosts the Profit-Led podcast, sharing growth strategies for bootstrap founders, and offers valuable insights on startup life and founder well-being on LinkedIn. The conversation delves into scaling product-led growth tech companies, Melissa’s journey toward building a lifestyle business, and her unique approach to redefining success on her own terms.

Chapters:

00:00 - Introduction
01:22 - Scaling Insights with Melissa Kwan
04:59 - "Scaling Tech Companies: Growth Path"
07:32 - Uncertain Investment in SEO
12:02 - "LinkedIn Strategy Amid Algorithm Shifts"
14:17 - Navigating Relationships in a PLG World
19:08 - Customer Churn Feedback Request
21:03 - Clear Prioritization and Trade-Offs
24:07 - Market Misunderstanding Inquiry
26:52 - Live Content: What Truly Needs It?
31:40 - "Persistence in Sales and Marketing"
34:31 - Lifestyle Business Decision: Moment or Gradual?
36:26 - Customers Over Investors
41:04 - Finding Freedom Through Self-Understanding
43:43 - The Mental Struggles of Founders
47:27 - Breaking Free from Traditional Expectations
50:03 - Defining Personal Meaning and Connection
52:40 - Outro

Key Takeawys:

eWebinar Platform Overview
Ideal Customer Profile for eWebinar
Challenges and Opportunities in Scaling
LinkedIn and SEO Strategies
Balancing PLG and Customer Relationships
Misunderstandings in the Market
Personal and Professional Growth as a CEO
Transformation and Happiness in Business

Quotes:

"Don't leave a thriving community to chase someone who doesn't value you. Focus on those who appreciate your presence."- Melissa Kwan

"Know your goals and choose your path wisely. Embrace the freedom to create the life you desire."- Scott Shagory

Connect with Melissa Kwan:
LinkedIn
Website

Connect with the Host Scott Shagory:
Website
LinkedIn
Email: scott@purplefinchgroup.com

Sponsor: Purple Finch Group
Call to Action: Visit eWebinar
Powered by: Heartcast Media]]>https://api.spreaker.com/episode/64611442Tue, 18 Mar 2025 08:30:07 +0000Scott ShagoryMelissa Kwan, cofounder and CEO of https://ewebinar.com/ , is transforming webinar automation by eliminating the repetitive strain of live sessions she describes as "soul crushing." In this episode of the Disciplined Troublemakers podcast, Scott...eWebinar , is transforming webinar automation by eliminating the repetitive strain of live sessions she describes as "soul crushing." In this episode of the Disciplined Troublemakers podcast, Scott Shagory explores how Melissa's innovative solutions enable technology leaders to scale their companies and boost profitability. Beyond eWebinar, Melissa cohosts the Profit-Led podcast, sharing growth strategies for bootstrap founders, and offers valuable insights on startup life and founder well-being on LinkedIn. The conversation delves into scaling product-led growth tech companies, Melissa’s journey toward building a lifestyle business, and her unique approach to redefining success on her own terms.

Chapters:

00:00 - Introduction
01:22 - Scaling Insights with Melissa Kwan
04:59 - "Scaling Tech Companies: Growth Path"
07:32 - Uncertain Investment in SEO
12:02 - "LinkedIn Strategy Amid Algorithm Shifts"
14:17 - Navigating Relationships in a PLG World
19:08 - Customer Churn Feedback Request
21:03 - Clear Prioritization and Trade-Offs
24:07 - Market Misunderstanding Inquiry
26:52 - Live Content: What Truly Needs It?
31:40 - "Persistence in Sales and Marketing"
34:31 - Lifestyle Business Decision: Moment or Gradual?
36:26 - Customers Over Investors
41:04 - Finding Freedom Through Self-Understanding
43:43 - The Mental Struggles of Founders
47:27 - Breaking Free from Traditional Expectations
50:03 - Defining Personal Meaning and Connection
52:40 - Outro

Key Takeawys:

eWebinar Platform Overview
Ideal Customer Profile for eWebinar
Challenges and Opportunities in Scaling
LinkedIn and SEO Strategies
Balancing PLG and Customer Relationships
Misunderstandings in the Market
Personal and Professional Growth as a CEO
Transformation and Happiness in Business

Quotes:

"Don't leave a thriving community to chase someone who doesn't value you. Focus on those who appreciate your presence."- Melissa Kwan

"Know your goals and choose your path wisely. Embrace the freedom to create the life you desire."- Scott Shagory

Connect with Melissa Kwan:
LinkedIn
Website

Connect with the Host Scott Shagory:
Website
LinkedIn
Email: scott@purplefinchgroup.com

Sponsor: Purple Finch Group
Call to Action: Visit eWebinar
Powered by: Heartcast Media]]>3164bootstrapfounders,contentcreation,ewebinar,linkedin,onboarding,podcastmarketing,productledgrowth,scalingchallenges,scalingtechcompanies,seofalsefullhttps://purplefinchgroup.com/podcast/building-conversational-commerce-in-latin-america-with-roberto-penacastro-ortega/
Quotes:

"Transitioning to exponential growth is achievable with less effort and stress."- Scott Shagory

"With millions of daily messages, we have the data to harness AI effectively."- Roberto Penacastro Ortega

Chapters:

00:00 - Introduction
01:30 - Future of Conversational Commerce
03:40 - Mobile-Only Challenges in CRM Markets
07:55 - Asynchronous vs. Real-Time Communication
12:19 - From Family Business to Tech Startup
16:53 - Rapid Startup Growth Strategy
20:35 - "Keys to Successful Team Dynamics"
21:52 - "Scaling Tech CEOs with Strategy"
25:59 - Unlocking Global Potential for SMBs
27:54 - Unlocking Implicit Genius
31:26 - Leadership Handoff Challenges and Opportunities
35:15 - Navigating Challenges and Transformative Moments
39:23 - Startup Challenges Outside the US
42:41 - LinkedIn's Global Connectivity Benefits
44:39 - Outro

Featured in this Episode:
Roberto (Roby) Penacastro Ortega is the founder and CEO of LeadSales. Founded in 2020, LeadSales is a CRM platform that helps businesses generate and manage leads. Their focus is helping small and medium businesses in LATAM manage all their potential sales via social media channels by centralizing leads into column chats.

Connect with Roby:
LinkedIn
Website

Connect with the Host: Scott Shagory
Website
LinkedIn
Email: scott@purplefinchgroup.com

Sponsor: Purple Finch Group
Call to Action: Visithttps://leadsales.io/en/
Powered by: Heartcast Media]]>https://api.spreaker.com/episode/64418275Wed, 05 Mar 2025 10:00:13 +0000Scott ShagoryIn this episode of the Disciplined Troublemakers podcast, host Scott Shagory speaks with Roberto Penacastro Ortega, founder and CEO of LeadSales. Since its inception in 2020, LeadSales has provided a CRM and conversational commerce platform that...
Quotes:

"Transitioning to exponential growth is achievable with less effort and stress."- Scott Shagory

"With millions of daily messages, we have the data to harness AI effectively."- Roberto Penacastro Ortega

Chapters:

00:00 - Introduction
01:30 - Future of Conversational Commerce
03:40 - Mobile-Only Challenges in CRM Markets
07:55 - Asynchronous vs. Real-Time Communication
12:19 - From Family Business to Tech Startup
16:53 - Rapid Startup Growth Strategy
20:35 - "Keys to Successful Team Dynamics"
21:52 - "Scaling Tech CEOs with Strategy"
25:59 - Unlocking Global Potential for SMBs
27:54 - Unlocking Implicit Genius
31:26 - Leadership Handoff Challenges and Opportunities
35:15 - Navigating Challenges and Transformative Moments
39:23 - Startup Challenges Outside the US
42:41 - LinkedIn's Global Connectivity Benefits
44:39 - Outro

Featured in this Episode:
Roberto (Roby) Penacastro Ortega is the founder and CEO of LeadSales. Founded in 2020, LeadSales is a CRM platform that helps businesses generate and manage leads. Their focus is helping small and medium businesses in LATAM manage all their potential sales via social media channels by centralizing leads into column chats.

Connect with Roby:
LinkedIn
Website

Connect with the Host: Scott Shagory
Website
LinkedIn
Email: scott@purplefinchgroup.com

Sponsor: Purple Finch Group
Call to Action: Visithttps://leadsales.io/en/
Powered by: Heartcast Media]]>2683businessgenius,ceo,crm,disciplinedtroublemakers,growthstrategy,heartcastmedia,leadership,startupcompanyfalsefullhttps://purplefinchgroup.com/podcast/ai-agent-opportunities-in-healthcare/
Prior to Autonomize AI, Ganesh helped scale AI companies such as Molecula and CognitiveScale and before that time spent at Dell and Intel.

Quotes
"Choose a meaningful problem, ensure people are willing to pay for the solution, and build a sustainable business." — Ganesh Padmahaban

"At the core of everything is the patient. By organizing their data and understanding their journey, we can revolutionize healthcare and create meaningful efficiencies." — Ganesh Padmahaban

Featured in this Episode:
Ganesh Padmahaban
LinkedIn: https://www.linkedin.com/in/padmanabhan
Website:https://autonomize.ai/

Sponsor:
Purple Finch Group

Host:
Scott Shagory
Email: scott@purplefinchgroup.com
Website: http://purplefinchgroup.com

Chapters:
00:00 - Introduction
03:36 - Healthcare's Unstructured Data Challenge
08:27 - Patient-Centric Health Data Platform
11:56 - AI's Role in Healthcare Relief
14:10 - "Conviction in Meaningful Problem Solving"
17:24 - Recruiting and Building Company Culture
22:38 - AI Impact and Misunderstandings
24:27 - "Delivering Clear, Real-World Value"
28:56 - Learning Through Customer Interaction
31:34 - Service for Others' Aspirations
34:59 - Balancing Tech and Sales Enablement
37:58 - CEO Evolution and Team Dynamics
42:27 - Resilience in Leadership Challenges
45:11 - Seeking Support for Aggressive Growth
46:32 - Hiring & Strategic Partnerships Focus
50:27 - Outro

Call to Action Links:
Visit http://Autonomize.ai

Powered by:http://heartcastmedia.com/]]>https://api.spreaker.com/episode/64251490Tue, 25 Feb 2025 13:00:07 +0000Scott ShagoryGanesh Padmanabhan is the founder and CEO of Autonomize AI, which utilizes AI Agents and Copilots in healthcare workflows by summarizing unstructured healthcare data for data-driven decision making and improved patient outcomes. Autonomize AI is...
Prior to Autonomize AI, Ganesh helped scale AI companies such as Molecula and CognitiveScale and before that time spent at Dell and Intel.

Quotes
"Choose a meaningful problem, ensure people are willing to pay for the solution, and build a sustainable business." — Ganesh Padmahaban

"At the core of everything is the patient. By organizing their data and understanding their journey, we can revolutionize healthcare and create meaningful efficiencies." — Ganesh Padmahaban

Featured in this Episode:
Ganesh Padmahaban
LinkedIn: https://www.linkedin.com/in/padmanabhan
Website:https://autonomize.ai/

Sponsor:
Purple Finch Group

Host:
Scott Shagory
Email: scott@purplefinchgroup.com
Website: http://purplefinchgroup.com

Chapters:
00:00 - Introduction
03:36 - Healthcare's Unstructured Data Challenge
08:27 - Patient-Centric Health Data Platform
11:56 - AI's Role in Healthcare Relief
14:10 - "Conviction in Meaningful Problem Solving"
17:24 - Recruiting and Building Company Culture
22:38 - AI Impact and Misunderstandings
24:27 - "Delivering Clear, Real-World Value"
28:56 - Learning Through Customer Interaction
31:34 - Service for Others' Aspirations
34:59 - Balancing Tech and Sales Enablement
37:58 - CEO Evolution and Team Dynamics
42:27 - Resilience in Leadership Challenges
45:11 - Seeking Support for Aggressive Growth
46:32 - Hiring & Strategic Partnerships Focus
50:27 - Outro

Call to Action Links:
Visit http://Autonomize.ai

Powered by:http://heartcastmedia.com/]]>3138ai,aiapplications,aiinmodernhealthcare,disciplinedtroublemakers,healthcare,podcastai,purplefinchfalsefullhttps://purplefinchgroup.com/podcast/unifying-proactive-cybersecurity-with-ketan-nilangekar/
Quotes

"Think of proactive cybersecurity measures as vaccines, inoculating your enterprise against digital threats." - Ketan Nilangekar

"Seamlessly adapting to new threats, our platform is designed to effortlessly accommodate emerging challenges in cybersecurity."- Ketan Nilangekar

Featured in this Episode

Ketan Nilangekar
CEO of ThreatWorx
LinkedIn: https://www.linkedin.com/in/ketan-nilangekar
Website:https://threatworx.io/

Chapters

00:00 - Introduction
01:08 - ThreatWorks: A Comprehensive Cybersecurity Solution
06:21 - Proactively Redesigning Threat Detection for Tax Offices
10:14 - Enterprises Must Combat Emerging Malware from GitHub
13:39 - AI is Essential for Managing Data Vulnerabilities
17:02 - Minimizing Noise to Effectively Protect Against Vulnerabilities
19:07 - CISOs Encounter Critical Security Challenges Daily
22:06 - Simplifying Threat Intelligence for Customer Clarity
28:04 - The Excitement of Building Tools and Overcoming Challenges
29:00 - Sharing Knowledge and Serving the Community
33:08 - The Innovative Journey Requires Confidence and Conviction
35:12 - Bootstrap Advantages: Time for Self-Discovery and Less Pressure
40:59 - Seeking Partnerships and Ideas for Consolidation
41:56 - Collaboration in Cybersecurity is Key to Success
43:32 - Outro

Powered by http://heartcastmedia.com/]]>https://api.spreaker.com/episode/63450767Fri, 17 Jan 2025 08:45:06 +0000Scott ShagoryKetan Nilangekar is the founder and CEO of ThreatWorx, which delivers a unified solution for proactive cybersecurity, combining application and container security, vulnerability and third-party risk management, and threat intelligence into one...
Quotes

"Think of proactive cybersecurity measures as vaccines, inoculating your enterprise against digital threats." - Ketan Nilangekar

"Seamlessly adapting to new threats, our platform is designed to effortlessly accommodate emerging challenges in cybersecurity."- Ketan Nilangekar

Featured in this Episode

Ketan Nilangekar
CEO of ThreatWorx
LinkedIn: https://www.linkedin.com/in/ketan-nilangekar
Website:https://threatworx.io/

Chapters

00:00 - Introduction
01:08 - ThreatWorks: A Comprehensive Cybersecurity Solution
06:21 - Proactively Redesigning Threat Detection for Tax Offices
10:14 - Enterprises Must Combat Emerging Malware from GitHub
13:39 - AI is Essential for Managing Data Vulnerabilities
17:02 - Minimizing Noise to Effectively Protect Against Vulnerabilities
19:07 - CISOs Encounter Critical Security Challenges Daily
22:06 - Simplifying Threat Intelligence for Customer Clarity
28:04 - The Excitement of Building Tools and Overcoming Challenges
29:00 - Sharing Knowledge and Serving the Community
33:08 - The Innovative Journey Requires Confidence and Conviction
35:12 - Bootstrap Advantages: Time for Self-Discovery and Less Pressure
40:59 - Seeking Partnerships and Ideas for Consolidation
41:56 - Collaboration in Cybersecurity is Key to Success
43:32 - Outro

Powered by http://heartcastmedia.com/]]>2617aicybersecurity,cybersecurity,datamanagement,disciplinedtroublemakers,proactivecybersecurity,threatworxfalsefullhttps://purplefinchgroup.com/podcast/go-to-market-strategies-that-scale-with-chris-kirsch/
Join us for valuable insights on scaling tech businesses. Let's dive in!

Quotes

"The journey of entrepreneurship can begin with a single part-time effort fueled by passion." - Chris Kirsch

"Building processes and systems from the start is key to sustainable growth." - Chris Kirsch

Featured in this Episode

Chris Kirsch
Linkedin: https://www.linkedin.com/in/ckirsch
Website: Cyber Marketing Clinic

Chapters

00:00 - Introduction
01:00 - Managing Complex Network Connections
07:00 - HD Moore on Metasploit and Cybersecurity
15:03 - Quick Product Demos Via Social Media
20:11 - Enhancing Retention Through Streamlined Research
23:51 - Importance of Experienced Directors for Growth
28:24 - Founders’ and VCs’ Incentive Alignment
36:17 - Defining Ideal Customer Profile (ICP)
41:54 - Emphasizing Low Pricing and User Experience
46:22 - Evaluating Customer Value Through Interviews
50:04 - Refining ICP and Market Strategy
57:58 - Challenges in Finding The Right Sales Leader
59:57 - Revenue from Series A Companies

Powered by http://heartcastmedia.com]]>https://api.spreaker.com/episode/63450545Tue, 14 Jan 2025 10:00:12 +0000Scott ShagoryWelcome back to The Disciplined Troublemakers. In this episode, we discuss successful tech company strategies with Chris Kirsch, Founder and CEO of the Cyber Marketing Clinic and former CEO of RunZero. Chris brings extensive expertise in product...
Join us for valuable insights on scaling tech businesses. Let's dive in!

Quotes

"The journey of entrepreneurship can begin with a single part-time effort fueled by passion." - Chris Kirsch

"Building processes and systems from the start is key to sustainable growth." - Chris Kirsch

Featured in this Episode

Chris Kirsch
Linkedin: https://www.linkedin.com/in/ckirsch
Website: Cyber Marketing Clinic

Chapters

00:00 - Introduction
01:00 - Managing Complex Network Connections
07:00 - HD Moore on Metasploit and Cybersecurity
15:03 - Quick Product Demos Via Social Media
20:11 - Enhancing Retention Through Streamlined Research
23:51 - Importance of Experienced Directors for Growth
28:24 - Founders’ and VCs’ Incentive Alignment
36:17 - Defining Ideal Customer Profile (ICP)
41:54 - Emphasizing Low Pricing and User Experience
46:22 - Evaluating Customer Value Through Interviews
50:04 - Refining ICP and Market Strategy
57:58 - Challenges in Finding The Right Sales Leader
59:57 - Revenue from Series A Companies

Powered by http://heartcastmedia.com]]>3791disciplinedtroublemakers,marketgrowth,marketing,marketscale,marketstrategy,marketupscaling,socialmedia,socialmediapromotionfalsefullhttps://purplefinchgroup.com/podcast/managing-it-services-and-cybersecurity-with-earl-foote-2/
Join us to gain insights into shaping the IT landscape and improving business operations. Let's dive in!

Quotes

"Regulated firms need strong cyber and compliance practices for annual audits." - Earl Foote

"Concentrate on your core competencies, and partner with experts for everything else." - Earl Foote

Featured in this Episode

Earl Foote
Linkedin: https://www.linkedin.com/in/earlfoote
Website: https://www.nexusitc.net/

Chapters

00:00 - Introduction
01:26 - Owning 20-25 Guitars Across Locations
04:57 - Tech Partnerships and Innovations
08:06 - Impact of Cybersecurity Compliance on Industries
10:05 - Innovative Solutions for Enhanced Cyber Compliance
15:52 - Cyber Practices: Essential for Compliance
19:34 - High-Growth Security Provider: 93% CAGR, Employee Praise
20:59 - Utah's Top MSP Expands Responsibly Nationwide
24:43 - Strategic Growth and Talent Search
29:34 - MSPs Explained: More Than Basic IT Support
32:30 - Collaborative Tech and Security Enhancements for Large Orgs
35:01 - Improving Tech Compliance for Clients
38:10 - Sales Empowerment, Not Fear-Based
41:35 - Visionary, Growth-Minded Leadership
47:42 - Meditation for Grounding Amid Challenges
49:39 - Growth Mindset and Humility Drive Success
51:57 - Leadership Growth Through Empowering Others
55:15 - Outro

Powered by http://heartcastmedia.com]]>https://api.spreaker.com/episode/63343037Tue, 07 Jan 2025 09:35:06 +0000Scott ShagoryWelcome back to The Disciplined Troublemakers. In this episode, we explore IT services and cybersecurity with Earl Foote, the founder and CEO of Nexus IT Consultants, a MSSP based in Utah and a 3x founder on the INC 5000 list.  Nexus IT Consultants...
Join us to gain insights into shaping the IT landscape and improving business operations. Let's dive in!

Quotes

"Regulated firms need strong cyber and compliance practices for annual audits." - Earl Foote

"Concentrate on your core competencies, and partner with experts for everything else." - Earl Foote

Featured in this Episode

Earl Foote
Linkedin: https://www.linkedin.com/in/earlfoote
Website: https://www.nexusitc.net/

Chapters

00:00 - Introduction
01:26 - Owning 20-25 Guitars Across Locations
04:57 - Tech Partnerships and Innovations
08:06 - Impact of Cybersecurity Compliance on Industries
10:05 - Innovative Solutions for Enhanced Cyber Compliance
15:52 - Cyber Practices: Essential for Compliance
19:34 - High-Growth Security Provider: 93% CAGR, Employee Praise
20:59 - Utah's Top MSP Expands Responsibly Nationwide
24:43 - Strategic Growth and Talent Search
29:34 - MSPs Explained: More Than Basic IT Support
32:30 - Collaborative Tech and Security Enhancements for Large Orgs
35:01 - Improving Tech Compliance for Clients
38:10 - Sales Empowerment, Not Fear-Based
41:35 - Visionary, Growth-Minded Leadership
47:42 - Meditation for Grounding Amid Challenges
49:39 - Growth Mindset and Humility Drive Success
51:57 - Leadership Growth Through Empowering Others
55:15 - Outro

Powered by http://heartcastmedia.com]]>3327cybersecurity,informationtechnology,internet,it,onlinesecurity,websecurity,websitefalsefullhttps://purplefinchgroup.com/podcast/buying-profitable-businesses-with-managing-partner-daniel-sweet/
Join us to enhance your business skills and position your company for success. Let's dive in!

Quotes

"In our ideal world, sales keep the operator constantly scrambling. That's the right level of growth." - Daniel Sweet

"If your profit is fine-tuned to break even and avoid taxes, that's great until you sell, because a multiple of zero is zero."  - Daniel Sweet

Featured in this Episode

Daniel Sweet
Linkedin:  https://www.linkedin.com/in/danielrsweet
Website:https://www.sweetviewpartners.com/
https://thekeyssummit.com/

Chapters
00:00- Introduction
07:19- Market Gaps & Bootstrapped Entrepreneurs
11:32- Struggles in Small Business Management
19:04- System Challenges & Instant Insights
22:34- Retaining Ownership: Strategy Discussion
24:25- Consequences of Poor Financial Planning
29:04- Exponential Growth: Contact Scott at Purple Finch
30:53- Leveraging Experience for Growth
35:47- Tech for Efficiency, Not Job Cuts
38:23- CRM & Staff Training for Success
39:37- Practical SaaS and Tech Strategies
44:40- Navigating Financial Uncertainties
46:27- Financial Focus for Successful Selling
50:40- Summit for Freedom & Happiness
52:49- Complimentary Speaker Access
57:20- Effective Tools for Small Businesses
59:24- Outro

Powered by http://heartcastmedia.com]]>https://api.spreaker.com/episode/60073056Mon, 20 May 2024 09:10:02 +0000Scott ShagoryWelcome back to The Disciplined Troublemakers. In this episode, we explore forecasting and financial systems for risk mitigation and business performance. Daniel shares a story of a startup with cash flow problems despite a successful product,...
Join us to enhance your business skills and position your company for success. Let's dive in!

Quotes

"In our ideal world, sales keep the operator constantly scrambling. That's the right level of growth." - Daniel Sweet

"If your profit is fine-tuned to break even and avoid taxes, that's great until you sell, because a multiple of zero is zero."  - Daniel Sweet

Featured in this Episode

Daniel Sweet
Linkedin:  https://www.linkedin.com/in/danielrsweet
Website:https://www.sweetviewpartners.com/
https://thekeyssummit.com/

Chapters
00:00- Introduction
07:19- Market Gaps & Bootstrapped Entrepreneurs
11:32- Struggles in Small Business Management
19:04- System Challenges & Instant Insights
22:34- Retaining Ownership: Strategy Discussion
24:25- Consequences of Poor Financial Planning
29:04- Exponential Growth: Contact Scott at Purple Finch
30:53- Leveraging Experience for Growth
35:47- Tech for Efficiency, Not Job Cuts
38:23- CRM & Staff Training for Success
39:37- Practical SaaS and Tech Strategies
44:40- Navigating Financial Uncertainties
46:27- Financial Focus for Successful Selling
50:40- Summit for Freedom & Happiness
52:49- Complimentary Speaker Access
57:20- Effective Tools for Small Businesses
59:24- Outro

Powered by http://heartcastmedia.com]]>3612business,disciplinedtroublemaker,entrepeneurship,finance,financialsuccess,speakerfreedomfalsefullhttps://purplefinchgroup.com/podcast/owning-your-tech-companys-financial-truth-with-anthony-nitsos/

Quotes

"Businesses empower individuals to fulfill responsibilities and care for loved ones effectively." - Anthony Nitsos

"Every decision impacts profit and cash flow. Understanding their origins improves effectiveness, especially for C-suite executives."- Anthony Nitsos


Featured in this Episode

Anthony Nitsos
LinkedIn: ​​ https://www.linkedin.com/in/anthonynitsos
Website: http://www.saasgurus.io/


Chapters

00:00 - Introduction
03:51 - Operations: Cash runway and sales growth vital
08:01 - Shorter CEO terms allow more focus
12:11 - Consistency in strategy and vision is crucial
14:42 - Understanding value of recurring revenue and evaluation
18:05 - Problem? Bring a solution, valuable for clients
23:03 - SaaS Gurus help CEOs price contracts strategically
24:28 - Negotiation involves determining what market will bear
27:32 - $500,000 ACV, $50,000 Contract: CFO's Focus
32:56 - Shifting to exponential growth, struggling VC-backed SaaS companies
36:10 - Valid product, strong market strategy crucial. Executing both
37:55 - CFO role extends beyond finance, sales, marketing
41:05 - Overcoming technical details to move forward successfully
44:35 - Exciting and dynamic place for teams and technology
54:44 - Outro

Powered byhttp://heartcastmedia.com]]>https://api.spreaker.com/episode/59487730Mon, 06 May 2024 09:00:04 +0000Scott ShagoryIn Episode 4 of The Disciplined Troublemakers, our exceptional guest Anthony Nitsos delves into the SaaS industry's evolution towards a targeted go-to-market approach. Explore product pricing strategies and negotiation dynamics, influenced by business...

Quotes

"Businesses empower individuals to fulfill responsibilities and care for loved ones effectively." - Anthony Nitsos

"Every decision impacts profit and cash flow. Understanding their origins improves effectiveness, especially for C-suite executives."- Anthony Nitsos


Featured in this Episode

Anthony Nitsos
LinkedIn: ​​ https://www.linkedin.com/in/anthonynitsos
Website: http://www.saasgurus.io/


Chapters

00:00 - Introduction
03:51 - Operations: Cash runway and sales growth vital
08:01 - Shorter CEO terms allow more focus
12:11 - Consistency in strategy and vision is crucial
14:42 - Understanding value of recurring revenue and evaluation
18:05 - Problem? Bring a solution, valuable for clients
23:03 - SaaS Gurus help CEOs price contracts strategically
24:28 - Negotiation involves determining what market will bear
27:32 - $500,000 ACV, $50,000 Contract: CFO's Focus
32:56 - Shifting to exponential growth, struggling VC-backed SaaS companies
36:10 - Valid product, strong market strategy crucial. Executing both
37:55 - CFO role extends beyond finance, sales, marketing
41:05 - Overcoming technical details to move forward successfully
44:35 - Exciting and dynamic place for teams and technology
54:44 - Outro

Powered byhttp://heartcastmedia.com]]>3286business,company,entrepreneurs,finance,financing,techcompany,technologyfalsefullhttps://purplefinchgroup.com/podcast/addressing-hallucinations-llms-you-can-trust-with-scott-cohen/

Quotes

"If we solely relied on AI, the spark of creativity would be lost. Instead, AI's true power lies in empowering us to reach new heights." - Scott Cohen

"Maintaining a human element in AI operations ensures guidance towards tasks and broader objectives." - Scott Cohen


Featured in this Episode

Scott Cohen
LinkedIn: ​​https://www.linkedin.com/in/scottncohen
Website: http://jaxon.ai/


Chapters

00:00 - Introduction
04:04 - Focus on Specific Industries for AI
09:46 - Verification for Token Prediction Models
11:35 - Hallucinations vs Inaccuracies in Transformer Models
15:39 - Efficient AI Building with DETAIL Tool Chain
19:39 - Cooking Skills: Learning and Adapting
20:19 - Enterprise Costs and Impact Inquiry
24:27 - Human-Driven Decision-Making
28:12 - Scott Shagory Interviews Scott Cohen on Fundraising
32:04 - Commercial vs. Government: Value Propositions
34:46 - Balancing Human Uniqueness with AI in Business
37:03 - Human-AI Communication in the Workplace
41:53 - Collaboration Issues in AI Project Failures
45:10 - Navigating Organizational Hierarchy Challenges
47:07 - Importance of Educational Outreach in Data Science Teams
52:50 - Conclusion]]>https://api.spreaker.com/episode/59487589Mon, 22 Apr 2024 09:00:05 +0000Scott ShagoryWelcome back to Disciplined Trouble Makers! In this episode, we'll dive into the AI world with Scott Cohen from Jackson AI, known for groundbreaking work with the Department of Defense. Scott explores AI's ROI, scalability, and the buzz around AI...

Quotes

"If we solely relied on AI, the spark of creativity would be lost. Instead, AI's true power lies in empowering us to reach new heights." - Scott Cohen

"Maintaining a human element in AI operations ensures guidance towards tasks and broader objectives." - Scott Cohen


Featured in this Episode

Scott Cohen
LinkedIn: ​​https://www.linkedin.com/in/scottncohen
Website: http://jaxon.ai/


Chapters

00:00 - Introduction
04:04 - Focus on Specific Industries for AI
09:46 - Verification for Token Prediction Models
11:35 - Hallucinations vs Inaccuracies in Transformer Models
15:39 - Efficient AI Building with DETAIL Tool Chain
19:39 - Cooking Skills: Learning and Adapting
20:19 - Enterprise Costs and Impact Inquiry
24:27 - Human-Driven Decision-Making
28:12 - Scott Shagory Interviews Scott Cohen on Fundraising
32:04 - Commercial vs. Government: Value Propositions
34:46 - Balancing Human Uniqueness with AI in Business
37:03 - Human-AI Communication in the Workplace
41:53 - Collaboration Issues in AI Project Failures
45:10 - Navigating Organizational Hierarchy Challenges
47:07 - Importance of Educational Outreach in Data Science Teams
52:50 - Conclusion]]>3198ai,aicontent,aimarketing,aitools,datascience,decisionmaking,disciplinedtroublemakers,scottshagoryfalsefullhttps://www.spreaker.com/episode/negotiating-with-a-psychological-edge-with-al-mcbride--58107516
Quotes

"Exercising bravery involves taking a step outside the familiar confines and expressing your needs with assertiveness."–Al Mcbride

"Negotiation is all about adopting better rituals, letting go of what doesn't serve you, and being mindfully aware." - Al Mcbride

Featured in this Episode

Al Mcbride
LinkedIn: https://www.linkedin.com/in/aliste/
Website: www.almcbride.com
Upcoming Book: https://almcbride.com/book/

Chapters
00:00 - Introduction
00:15 - The Pressure on Business Leaders: Balancing Emotions in Negotiation
10:06 - Mutual Benefit in Negotiation: Going Beyond Self-Interest
11:52 - Embracing Vulnerability: Clear Goals and Authentic Negotiation
20:48 - The Significance of Strategy: Navigating Negotiation with Clarity
26:12 - Role and Identity in Negotiation: Taking Ownership of Emotional State
29:34 - Operational Fitness with Purple Finch Group: Assisting CEOs
38:16 - The Cost Breakdown Gap: Crucial Knowledge for Salespeople
44:06 - Enlightenment Through Philosophy: Personal Growth and Methods
45:30 - Gender Differences in Negotiation: Personal vs. Cause-driven
51:51 - Condensed Wisdom: Books as Vessels of Knowledge
56:17 - Honesty and Caution: Building Strong Interpersonal Relations
01:00:35 - Conclusion

Produced by heartcastmedia.com]]>https://api.spreaker.com/episode/58107516Mon, 22 Jan 2024 10:05:01 +0000Scott ShagoryIn this episode of "Disciplined Trouble Makers," negotiation and communication coach Al Mcbride shares valuable insights on the complexities of negotiation. Discover the impact of emotions and mindset, the value of trust and rapport, and effective...
Quotes

"Exercising bravery involves taking a step outside the familiar confines and expressing your needs with assertiveness."–Al Mcbride

"Negotiation is all about adopting better rituals, letting go of what doesn't serve you, and being mindfully aware." - Al Mcbride

Featured in this Episode

Al Mcbride
LinkedIn: https://www.linkedin.com/in/aliste/
Website: www.almcbride.com
Upcoming Book: https://almcbride.com/book/

Chapters
00:00 - Introduction
00:15 - The Pressure on Business Leaders: Balancing Emotions in Negotiation
10:06 - Mutual Benefit in Negotiation: Going Beyond Self-Interest
11:52 - Embracing Vulnerability: Clear Goals and Authentic Negotiation
20:48 - The Significance of Strategy: Navigating Negotiation with Clarity
26:12 - Role and Identity in Negotiation: Taking Ownership of Emotional State
29:34 - Operational Fitness with Purple Finch Group: Assisting CEOs
38:16 - The Cost Breakdown Gap: Crucial Knowledge for Salespeople
44:06 - Enlightenment Through Philosophy: Personal Growth and Methods
45:30 - Gender Differences in Negotiation: Personal vs. Cause-driven
51:51 - Condensed Wisdom: Books as Vessels of Knowledge
56:17 - Honesty and Caution: Building Strong Interpersonal Relations
01:00:35 - Conclusion

Produced by heartcastmedia.com]]>3681almcbrdige,communication,intellect,negotiation,philosophy,purplefinch,relationsfalsefullhttps://purplefinchgroup.com/podcast/defining-cybersecurity-in-economic-terms-with-ceo-joe-saunders-2/
Quotes

"You want to make other people look good. Whether it's your customer, a colleague in a meeting, or anyone else, the goal is to be selfless and create opportunities for others to shine." -Joe Saunders

"One of the most important things that I've learned is having a really good framework about who you are and who your company is." -Joe Saunders

Featured in this Episode

Joe Saunders
CEO, RunSafe Security
LinkedIn: https://www.linkedin.com/in/joesaunders/
Website: www.runsafesecurity.com
Podcast: https://pod.co/lessons-from-the-school-of-cyber-hard-knocks

Chapters

00:00 - Introduction
00:15 - Building Resilient Software: RunSafe's Mission to Eliminate Vulnerabilities
05:27 - Adapting Economically in an Uncertain Landscape
09:35 - Shaping Intent and Navigating Economic Perspectives
14:12 - Aligning Efforts and Educating on Vulnerabilities
15:05 - Selling the Future: The Complex Process and Buyer Education
18:41 - Discussing Gremlin's Solutions for Tech Companies
24:32 - Cash Flow Positive and Yearning for Growth Opportunities
27:08 - The Importance of Effort: Going Above or Below the Line
31:27 - Shifting Towards Open Source: Software Trends in Embedded Devices
34:13 - The Open versus Closed Source Debate: Perspectives and Insights
37:50 - The Art of Improv: Making Others Shine in Collaboration
41:09 - Embracing Mistakes and Fostering Resilience in a Learning Culture
47:14 - Learning through Experience: Structure and Risk-taking in
53:01 - Conclusion

Produced by Heartcast Media
http://www.heartcastmedia.com]]>https://api.spreaker.com/episode/58107107Mon, 08 Jan 2024 10:00:03 +0000Scott ShagoryIn this episode of "Disciplined Trouble Makers," host Scott Shagory engages in a captivating conversation with Joe Saunders, the CEO and founder of RunSafe Security. Together, they delve into the dynamic world of cybersecurity and tech...
Quotes

"You want to make other people look good. Whether it's your customer, a colleague in a meeting, or anyone else, the goal is to be selfless and create opportunities for others to shine." -Joe Saunders

"One of the most important things that I've learned is having a really good framework about who you are and who your company is." -Joe Saunders

Featured in this Episode

Joe Saunders
CEO, RunSafe Security
LinkedIn: https://www.linkedin.com/in/joesaunders/
Website: www.runsafesecurity.com
Podcast: https://pod.co/lessons-from-the-school-of-cyber-hard-knocks

Chapters

00:00 - Introduction
00:15 - Building Resilient Software: RunSafe's Mission to Eliminate Vulnerabilities
05:27 - Adapting Economically in an Uncertain Landscape
09:35 - Shaping Intent and Navigating Economic Perspectives
14:12 - Aligning Efforts and Educating on Vulnerabilities
15:05 - Selling the Future: The Complex Process and Buyer Education
18:41 - Discussing Gremlin's Solutions for Tech Companies
24:32 - Cash Flow Positive and Yearning for Growth Opportunities
27:08 - The Importance of Effort: Going Above or Below the Line
31:27 - Shifting Towards Open Source: Software Trends in Embedded Devices
34:13 - The Open versus Closed Source Debate: Perspectives and Insights
37:50 - The Art of Improv: Making Others Shine in Collaboration
41:09 - Embracing Mistakes and Fostering Resilience in a Learning Culture
47:14 - Learning through Experience: Structure and Risk-taking in
53:01 - Conclusion

Produced by Heartcast Media
http://www.heartcastmedia.com]]>3225cybersecurity,cyberspace,disciplinedtroublemakers,innovation,internet,techleaders,technologyfalsefullhttps://www.spreaker.com/episode/pilot-episode--56726836
Join me, your host, Scott Shagory, as we dive headfirst into the dynamic universe of technology CEOs and their incredible stories of scaling, profitability, and successful exits.

In this weekly show, we'll unravel the secrets of visionary leaders who dared to challenge the status quo, disrupt industries, and build extraordinary companies – all on their own terms.

Tune in to gain exclusive insights that will empower tech CEOs and leaders to elevate their game and drive real impact in their organizations.

Are you ready to become a disciplined troublemaker and make waves in the tech world? Then don't miss a single episode of this podcast!]]>https://api.spreaker.com/episode/56726836Thu, 07 Sep 2023 16:41:04 +0000Scott ShagoryGet ready to embark on a journey into the world of tech innovation and entrepreneurship with the debut episode of the Disciplined Troublemakers Podcast! Join me, your host, Scott Shagory, as we dive headfirst into the dynamic universe of technology...
Join me, your host, Scott Shagory, as we dive headfirst into the dynamic universe of technology CEOs and their incredible stories of scaling, profitability, and successful exits.

In this weekly show, we'll unravel the secrets of visionary leaders who dared to challenge the status quo, disrupt industries, and build extraordinary companies – all on their own terms.

Tune in to gain exclusive insights that will empower tech CEOs and leaders to elevate their game and drive real impact in their organizations.

Are you ready to become a disciplined troublemaker and make waves in the tech world? Then don't miss a single episode of this podcast!]]>121falsefull